Sodium Hydroxide → HCID 58246321, compound

HRID 1850880Notes

Reaction equation

HRID 1850880 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH:11][C:12]([C:14]2([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[CH2:17][CH2:16][CH2:15]2)=O)=[CH:5][CH:4]=1.P(Cl)(Cl)([Cl:26])=O.[OH-].[Na+]>>[Cl:26][C:20]1[N:19]=[C:18]([C:14]2([C:12]3[C:7]4[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:8]=4)[CH2:9][CH2:10][N:11]=3)[CH2:17][CH2:16][CH2:15]2)[CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 58246336HCID 58246336, compound

Product 1

HCID 58246321HCID 58246321, compound

Procedure

N-[2-(4-methoxyphenyl)ethyl]-1-(pyridin-2-yl)cyclobutanecarboxamide (679 mg, 1.969 mmol) was reacted with phosphorusoxychloride (2.7 ml, 29.5 mmol) in the microwave at 140° C. for 60 min. The reaction mixture was poured on ice water. After 10 min 10% aqueous sodium hydroxide solution was added until pH 8 was reached. The aqueous layer was extracted with dichloromethane. The combined extracts were dried (MgSO4), concentrated in vacuo and the crude product was purified by flash chromatography (silica, dichloromethane, methanol). Yield: 560 mg (1.71 mmol, 87%).

Workup

  1. additionThe reaction mixture was poured on ice water
  2. extractionThe aqueous layer was extracted with dichloromethane
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customthe crude product was purified by flash chromatography (silica, dichloromethane, methanol)

Sources & evidence

ORD record
ord-048d5e4ab2da43c5ab42e675d914ed82
Source dataset
uspto-grants-2015_02
Patent number
US08957089B2

Reaction notes

Loading…